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They first meet in the ladies' room at MacLaren's Pub in The Pineapple Incident. Having just got out of a two-year relationship, she decide to hook up with the first guy she sees. Just then, Barney makes an appearance at their table, but she dismisses him. Later, drunk Ted starts singing out loud in the bar on top of a table not far from where she and her friends are sitting. She finds him cute and laughs at him when he falls off the table top.

Later that night, Ted meets Trudy in the ladies' room where he went to try and throw up. After a brief conversation, she gives him her number, and Ted calls her soon after. She hooks up with him that night but climbs down the fire escape from Ted's bedroom the next morning, but not before leaving a pineapple in Ted's room and re-counting the night's events. It is then that the narrator tells us that Ted called her a few days later, and she did not answer her phone.

In Third Wheel, she bumps into Ted again at MacLaren's. A few minutes later, college friend Rachel bumps into her, and the two reminisce with each other. The two girls show signs of being attracted to Ted, and they express the idea of having a long-fantasized threesome with him. Ted, however, bails out at the concrete prospect of the threesome, which would earn him Barney's three-way belt. Just as he's about to send the girls away, he decides to go for it, but by then, the girls have gone to Marshall and Lily's room. Whether Ted had the threesome or not remains a mystery to this day, since he has never talked about it. He never claimed the Threesome Belt, which Barney later became worthy of himself.